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When you see Maserone at the beginning of that shot, before they meet for the second time, he is nervous as hell. Plus, Tony threw him off guard with the hug, and so its like he responded with a flattering comment, because it seemed that Tony was actually pleased that Jack was in his company. I really thought there was a lot of substance in this episode, and I thought it was great

the "take off your hat" comment is becuase tony seems to dislike people wearing hats at restaurants. masarone gives the excuse that he is having a hair treatment (rogaine i think). that's why he tells him later "nothing to loose your hair over".

tony takes out massarone and feels guilty about it because he doesn't have proof other than the weight remark. and that's why he gets rid of the painting. in the bathroom scene he looks at himself in the mirror and realizes that massarone is kissing ass.

however, i did not like how this episode was handled (tina made a lil worth while <img src=http://www.ezboard.com/images/emoticons/tongue.gif ALT=":p"> ). but we never got to see the hit. its not the violence, but how did the hit take place? did tony do it? most likely but after the way tony spoke to him massarone would have been cautious to meet with tony wthout the fbi nearby. did he follow him secretly?

and is the fbi that stupid! they know tony is exteremely cautious yet they park suspiciously in plain view.

Tony has done wetwork before - Pussy, the Bevolacqua kid (the one who shot Christopher), and some guy at the marina ( I forget why, but Tony blasted him several times and had chains and cinder blocks ready in the back of his car). For Tony to whack someone at this stage of his life would be foolish, but he has made judgement errors before. It would have been nice if they would have shown the hit and let everyone know who did what. The smart choice would have been Christopher, but Chris is pretty sloppy when it comes to hits.

I agree with you. Tony knew he wasn't for real when he asked him if he was losing weight. Tony knew it wasn't true and therefore he wouldn't have any reason to say it, unless he was nervous and trying to score points with him. Also, the wire might have been under his hat. Note that he didn't remove it when Tony told him to take it off in the restaurant. The feds probably suspected Tony might pat him down, so the wire was placed under the hat. I think Tony became suspicious of him after the weight comment.

Tony threw away the painting not because he felt guilt about getting rid of Massarone. The Rat Pack were these classic film stars. There's nostalgia involved there concerning those movie stars as well as the class or '04 who are coming out of the woodworks. Tony probably expected things to be just like they were with Blundetto and him before jailtime. Tony throwing away the painting symbolized two things: his disgust with just how false Masserone's gesture was, as well as his realization that the Rat Pack doesn't exist in Tony's world anymore. He's the boss. He said it himself. Everyone has to treat him differently. He can no longer be "just one of the guys." That, and Blundetto trying to go straight further drives Tony away from...well, his mob crew, as well as Tony's fantasy of being part of a recently released Rat Pack.

Rat Pack probably also refers to, well, all the people in this episode ratting everyone else out. There's Masserone, Albert?, and Adrianna in that rat pack.